Plot synopsis
Miles is a grumpy, overweight novelist-cum-middle-school English teacher
desperately trying to find a publisher for his work -- and thus far
failing. His personal life's not so hot either; though divorced, he's
still kind of hung up on his ex-wife. Just about the only thing that
brings genuine joy to his sad existence is his love of fine wine. So as
his old buddy Jack gets ready to tie the knot, Miles decides that the
coolest gift he could give as best man is to treat Jack to a weeklong
trip through California wine country. Jack is Miles' polar opposite;
he's a D-list actor who still gets recognized for a soap opera role he
did way back when, though despite the downward trajectory of his career,
he remains as cocksure caddish as ever, all big blond swagger and toothy
grin. Jack's not all that into the wine thing; his eyes tend to glaze
over whenever Miles waxes rhapsodic about varietals and vintages. But
like Miles, he's looking forward to their trip: he sees it as a last
chance to score with as many ladies as possible, before marriage puts a
damper on his womanizing ways. Generous guy that he is, though, Jack's
not making this trip all about him; his groom's gift to Miles is a
promise to get his party-pooper, stick-in-the-mud buddy laid. Things
look promising for both pals when they meet two local lovelys: sexy
single mom Stephanie, who seems like the perfect fling for Jack, and
sensitive Maya, who just may be the one to bring Miles out of his shell.

Review
Some people have a hard time liking stories about people who aren't
"good" folks. If this is you, Sideways is likely to vex
you mightily. Protagonist Miles, to be honest, isn't all that nice a
guy. He drinks too much, and sometimes says nasty things, and can be
kind of pretentious; he stops by for a visit with his mom mostly to
steal some cash from her. But the amazing thing about Sideways is
that if you can get past all that, it's hard not to sympathize with
Miles. Partly this is because so much of Miles' miserableness is
directed at Miles himself. But mostly it's because Miles is played by
Paul Giamatti, who's such a refreshingly schlubby, ordinary looking guy
in the sea of perfect Hollywood bodies that it always makes me happy to
see him onscreen. Even if he doesn't remind you of yourself (and that's
probably a good thing), Miles seems like someone you could know in real
life. He's likeably unlikeable, eminently so, because he's so human.
Giamatti's face does an amazing job of revealing what's going on in
Miles' head; when Miles acts like a jerk, it's painfully obvious that
there's no one who feels worse about it than Miles himself. He wants to
be a better guy than he is -- and hey, which one of us can't identify
with that? It's his very flaws that make you root for him as he
tentatively opens up to the lovely Maya; in her company, you get
glimpses of the Miles he could be -- a happier, more confident Miles, a
bigger, less petty person. Fortunately, director Alexander Payne's too
good a director to let this turn into a mushy tale of redemption;
instead, what we get is a movie that's the perfect balance of funny and
sad, wicked and wonderful. It's a bittersweet treat that goes down nice
and easy, but then leaves you with an unexpected emotional punch.